Potassium Carbonate → tert-butyl 4-{4-[7-amino-2-(1-benzothiophen-7-yl)furo[2,3-c]pyridine-4-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 7-benzothiophene boronic acid, 4-[4-(7-amino-2-chloro-furo[2,3-c]pyridin-4-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 359 μmol), Pd(dppf)Cl2 (2.63 mg, 3.59 μmol), K2CO3, (74.4 mg, 538 μmol) in 1,4-dioxane (1.96 mL), and H2O (647 μL) was degassed and refilled with argon (3×). The reaction was heated in a microwave reactor at 100° C. for 70 min. The reaction was diluted with water, extracted with EtOAc (3×) and the combined extracts were dried over Na2SO4, then concentrated in vacuo to give a solid. The solid was purified by flash chromatography (60-100% EtOAc:hexanes) to afford 96 mg (64%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 8.03 (d, J=7.33 Hz, 1 H), 7.88-7.99 (m, 3 H), 7.75 (s, 1 H), 7.61 (d, J=5.31 Hz, 1 H), 7.56 (t, J=7.71 Hz, 1 H), 7.50 (d, J=5.56 Hz, 1 H), 7.44 (s, 1 H), 5.53 (br s, 2 H), 4.25-4.48 (m, 3 H), 2.90-3.01 (m, 2 H), 2.24 (d, J=15.16 Hz, 2 H), 1.97-2.11 (m, 2 H), 1.51 (s, 9 H); MS (ESI): 516.16 [M+H]+; HPLC tR=2.66 min.

Provenance & Evidence